N,N-Dimethylformamide

Name: <I>N,N</I>-Dimethylformamide
Brand: SIAL

anhydrous, 99.8%

Synonym(s):

DMF, NSC 5356

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About This Item

Linear Formula:

HCON(CH₃)₂

CAS Number:

68-12-2

Molecular Weight:

73.09

Beilstein:

605365

EC Number:

200-679-5

MDL number:

MFCD00003284

UNSPSC Code:

12352111

PubChem Substance ID:

57647999

NACRES:

NA.21

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grade

anhydrous

Quality Level

300

vapor density

2.5 (vs air)

vapor pressure

2.7 mmHg ( 20 °C)

Assay

99.8%

form

liquid

autoignition temp.

833 °F

expl. lim.

15.2 %

impurities

<0.005% water

evapn. residue

<0.0005%

refractive index

n20/D 1.430 (lit.)

pH

7 (20 °C, 200 g/L)

bp

153 °C (lit.)

mp

−61 °C (lit.)

density

0.944 g/mL (lit.)

SMILES string

[H]C(=O)N(C)C

InChI

1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3

InChI key

ZMXDDKWLCZADIW-UHFFFAOYSA-N

General description

N,N-Dimethylformamide (DMF) is the commonly employed solvent for chemical reactions. DMF is a useful solvent employed for the isolation of chlorophyll from plant tissues. It is widely employed reagent in organic synthesis. It plays multiple roles in various reactions such as solvent, dehydrating agent, reducing agent as well as catalyst. It is a multipurpose building block for the synthesis of compounds containing O, -CO, -NMe₂, -CONMe₂, -Me, -CHO as functional groups.

N,N-Dimethylformamide is a polar solvent commonly used in organic synthesis. It also acts as a multipurpose precursor for formylation, amination, aminocarbonylation, amidation and cyanation reactions.

Application

N,N-Dimethylformamide (anhydrous) has been used as solvent for the synthesis of cytotoxic luteinizing hormone-releasing hormone (LH-RH) conjugate AN-152 (a chemotherapeutic drug) and fluorophore C625 [4-(N,N-diphenylamino)-4′-(6-O-hemiglutarate)hexylsulfinyl stilbene]. It may be employed as solvent medium for the various organic reduction reactions.

DMF has been used as a solvent in the following processes:

Multi-step synthesis of L-azidohomoalanine (L-Aha) during the substitution of the mesylate by sodium azide.
Synthesis of phosphine-FLAG^®, a detection reagent for metabolic labeling of glycans.
Synthesis of per-O-acetylated 6-azidofucose, a per-O-acetylated azido sugar.

Solvent for many hydrophobic organic compounds.